Ammonia → (4s)-4-(5-Phenylpyridin-2-yloxy)-1-azatricyclo[3.3.1.13,7]decane p-toluenesulfonate

Reaktionsgleichung

Br[C:2]1[CH:3]=[CH:4][C:5]([O:8][C@@H:9]2[CH:16]3[CH2:17][N:12]4[CH2:13][CH:14]([CH2:18][CH:10]2[CH2:11]4)[CH2:15]3)=[N:6][CH:7]=1.[C:19]1(B(O)O)[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.[CH3:28][C:29]1[CH:30]=[CH:31][C:32]([S:35]([OH:38])(=[O:37])=[O:36])=[CH:33][CH:34]=1.N>>[C:29]1([CH3:28])[CH:30]=[CH:31][C:32]([S:35]([OH:38])(=[O:36])=[O:37])=[CH:33][CH:34]=1.[C:19]1([C:2]2[CH:3]=[CH:4][C:5]([O:8][C@@H:9]3[CH:16]4[CH2:17][N:12]5[CH2:13][CH:14]([CH2:18][CH:10]3[CH2:11]5)[CH2:15]4)=[N:6][CH:7]=2)[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Komponenten

Edukt 4

HCID 222Ammonia

HCID 6101p-Toluenesulfonic acid

HCID 66827Phenylboronic Acid

HCID 24990114(4s)-4-(5-Bromopyridin-2-yloxy)-1-azatricyclo[3.3.1.13,7]decane

Produkt 1

HCID 86621319(4s)-4-(5-Phenylpyridin-2-yloxy)-1-azatricyclo[3.3.1.13,7]decane p-toluenesulfonate

Versuchsvorschrift

The free base of the title compound was prepared from the product of Example 10C (45 mg, 0.14 mmol) and phenylboronic acid (25 mg, 0.20 mmol) according to Method F, and converted to the p-toluenesulfonate salt using the procedure of Method H: 1H NMR (300 MHz, methanol-D4) δ ppm 1.94 (d, J=13.2 Hz, 2H), 2.20 (s, 1H), 2.36 (s, 5H), 2.41 (s, 1H), 2.57 (s, 2H), 3.58 (s, 2H), 3.70 (s, 4H), 5.47 (t, J=3.4 Hz, 1H), 7.09 (d, J=8.5 Hz, 1H), 7.22 (d, J=7.8 Hz, 2H), 7.30-7.41 (m, 1H), 7.42-7.51 (m, 2H), 7.56-7.63 (m, 2H), 7.67-7.75 (m, 2H), 8.07 (dd, J=8.6, 2.5 Hz, 1H), 8.40 (d, J=2.4 Hz, 1H). MS (DCI/NH3) m/z=307 (M+H)+; Anal. Calcd. for C20H22N2O.1.3C7H8O3S.0.5H2O: C, 64.81; H, 6.24; N, 5.19 Found: C, 64.77; H, 6.30; N, 5.15.